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trans-Cyclooctenes as Halolactonization Catalysts.

Shunsuke Einaru1, Kenta Shitamichi1, Tagui Nagano1

  • 1Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, Kyoto, 615-8510, Japan.

Angewandte Chemie (International Ed. in English)
|August 31, 2018
PubMed
Summary

Trans-cyclooctenes efficiently catalyze halolactonizations, such as bromolactonizations and iodolactonizations. This study demonstrates the first catalytic application of trans-cyclooctenes, highlighting the importance of their framework and substituents for performance.

Keywords:
Lewis basehalolactonizationorganocatalyststrained olefinstrans-cyclooctene

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Strained olefins are valuable synthetic intermediates.
  • Halolactonization reactions are important for synthesizing cyclic compounds.
  • Catalysis by strained cyclic olefins has not been previously demonstrated.

Purpose of the Study:

  • To investigate the potential of trans-cyclooctenes as catalysts for halolactonization reactions.
  • To evaluate the influence of the trans-cyclooctene framework and its substituents on catalytic efficiency.

Main Methods:

  • Utilized trans-cyclooctenes as catalysts in bromolactonization and iodolactonization reactions.
  • Systematically varied substituents on the trans-cyclooctene framework to assess their impact.

Main Results:

  • Trans-cyclooctenes demonstrated high catalytic efficiency in both bromolactonization and iodolactonization.
  • The specific framework of trans-cyclooctenes was crucial for achieving excellent catalytic performance.
  • Substituents on the trans-cyclooctene ring significantly influenced the reaction efficiency.

Conclusions:

  • This work presents the first successful catalytic application of trans-cyclooctenes.
  • Trans-cyclooctenes are effective catalysts for halolactonization reactions.
  • The structural features of trans-cyclooctenes are key determinants of their catalytic activity.